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Foldable ophthalmic and otorhinolaryngological device materials

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US20030130460A1
US20030130460A1 US10350993 US35099303A US2003130460A1 US 20030130460 A1 US20030130460 A1 US 20030130460A1 US 10350993 US10350993 US 10350993 US 35099303 A US35099303 A US 35099303A US 2003130460 A1 US2003130460 A1 US 2003130460A1
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materials
material
monomer
device
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US6653422B2 (en )
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Charles Freeman
Douglas Schlueter
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Novartis AG
Pfizer Inc
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Pfizer Inc
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    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS, OR APPARATUS
    • G02B1/00Optical elements characterised by the material of which they are made
    • G02B1/04Optical elements characterised by the material of which they are made made of organic materials, e.g. plastics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION, OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS, OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS, OR SURGICAL ARTICLES
    • A61L27/00Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/14Macromolecular materials
    • A61L27/16Macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/26Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/30Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS, OR APPARATUS
    • G02B1/00Optical elements characterised by the material of which they are made
    • G02B1/04Optical elements characterised by the material of which they are made made of organic materials, e.g. plastics
    • G02B1/041Lenses
    • G02B1/043Contact lenses
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61FFILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, E.G. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2/00Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
    • A61F2/02Prostheses implantable into the body
    • A61F2/14Eye parts, e.g. lenses, corneal implants; Implanting instruments specially adapted therefor; Artificial eyes
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61FFILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, E.G. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2/00Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
    • A61F2/02Prostheses implantable into the body
    • A61F2/14Eye parts, e.g. lenses, corneal implants; Implanting instruments specially adapted therefor; Artificial eyes
    • A61F2/145Corneal inlays, onlays, or lenses for refractive correction
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61FFILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, E.G. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2/00Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
    • A61F2/02Prostheses implantable into the body
    • A61F2/14Eye parts, e.g. lenses, corneal implants; Implanting instruments specially adapted therefor; Artificial eyes
    • A61F2/16Intraocular lenses

Abstract

Disclosed are soft, high refractive index, acrylic materials having an elongation of at least 150%. These materials, especially useful as intraocular lens materials, contain an aryl acrylic hydrophobic monomer as the single principal device-forming monomer. In addition to their use as intraocular lens materials, the present materials are also suitable for use in other ophthalmic or otorhinolaryngological devices, such as contact lenses, keratoprostheses, corneal inlays or rings; otological ventilation tubes and nasal implants.

Description

  • [0001]
    This application is a continuation of U.S. Ser. No. 09/645,669, filed Aug. 23, 2000, which claims priority from U.S. Provisional Application, U.S. Serial No. 60/152,622 filed Sep. 7, 1999.
  • FIELD OF THE INVENTION
  • [0002]
    This invention is directed to acrylic device materials. In particular, this invention relates to soft, high refractive index acrylic device materials particularly suited for use as intraocular lens (“IOL”) materials.
  • BACKGROUND OF THE INVENTION
  • [0003]
    With the recent advances in small-incision cataract surgery, increased emphasis has been placed on developing soft, foldable materials suitable for use in artificial lenses. In general, these materials fall into one of three categories: hydrogels, silicones, and acrylics.
  • [0004]
    In general, hydrogel materials have a relatively low refractive index, making them less desirable than other materials because of the thicker lens optic necessary to achieve a given refractive power. Silicone materials generally have a higher refractive index than hydrogels, but tend to unfold explosively after being placed in the eye in a folded position. Explosive unfolding can potentially damage the corneal endothelium and/or rupture the natural lens capsule. Acrylic materials are desirable because they typically have a high refractive index and unfold more slowly or controllably than silicone materials.
  • [0005]
    U.S. Pat. No. 5,290,892 discloses high refractive index, acrylic materials suitable for use as an IOL material. These acrylic materials contain, as principal components, two aryl acrylic monomers. They also contain a cross-linking component. The lOLs made of these acrylic materials can be rolled or folded for insertion through small incisions.
  • [0006]
    U.S. Pat. No. 5,331,073 also discloses soft acrylic IOL materials. These materials contain as principal components, two acrylic monomers which are defined by the properties of their respective homopolymers. The first monomer is defined as one in which its homopolymer has a refractive index of at least about 1.50. The second monomer is defined as one in which its homopolymer has a glass transition temperature less than about 22° C. These IOL materials also contain a cross-linking component. Additionally, these materials may optionally contain a fourth constituent, different from the first three constituents, which is derived from a hydrophilic monomer. These materials preferably have a total of less than about 15% by weight of a hydrophilic component.
  • [0007]
    U.S. Pat. No. 5,693,095 discloses foldable ophthalmic lens materials comprising a total of at least 90% by weight of only two principal lens-forming monomers. One lens-forming monomer is an aryl acrylic hydrophobic monomer. The other lens-forming monomer is a hydrophilic monomer. The lens materials also comprise a cross-linking monomer and optionally comprise a UV absorber, polymerization initiators, reactive UV absorbers and reactive blue-light absorbers.
  • SUMMARY OF THE INVENTION
  • [0008]
    Improved soft, foldable acrylic materials which are particularly suited for use as lOLs, but which are also useful as other ophthalmic or otorhinoloaryngological devices, such as contact lenses, keratoprostheses, corneal rings or inlays, otological ventilation tubes and nasal implants have now been discovered. These materials contain only one principal lens-forming component: an aryl acrylic hydrophobic monomer. The materials of the present invention comprise at least about 80% by weight of the principal monomeric component. The remainder of the material comprises a cross-linking monomer and optionally one or more additional components selected from the group consisting of UV-light absorbing compounds and blue-light absorbing compounds.
  • [0009]
    Among other factors, the present invention is based on the finding that acrylic copolymers suitable for use as foldable IOL materials can be synthesized using only one principal aryl acrylic hydrophobic monomer, reducing or eliminating difficulties, such as physico/chemical heterogeneity, associated with curing copolymers that contain two or more principal device-forming monomers.
  • DETAILED DESCRIPTION OF THE INVENTION
  • [0010]
    The ophthalmic or otorhinolaryngological device materials of the present invention comprise only one principal device-forming monomer. For convenience, the device-forming monomer may be referred to as a lens-forming monomer, particularly with reference to an IOL. The materials of the present invention, however, are also suitable for use as other ophthalmic or otorhinolaryngological devices such as contact lenses, keratoprostheses, corneal inlays or rings, otological ventilation tubes and nasal implants.
  • [0011]
    The aryl acrylic hydrophobic monomers suitable for use as the sole lens-forming monomer in the materials of the present invention have the formula
  • [0012]
    wherein: A is H, CH3, CH2CH3, or CH2OH;
  • [0013]
    B is (CH2)m or [O(CH2)2]n;
  • [0014]
    C is (CH2)w;
  • [0015]
    m is 2-6;
  • [0016]
    n is 1-10;
  • [0017]
    Y is nothing, O, S, or NR, provided that if Y is O, S, or NR, then B is (CH2)m;
  • [0018]
    R is H, CH3, CnH2n+1 (n=1-10), iso-OC3H7, C6H5, or CH2C6H5;
  • [0019]
    w is 0-6, provided that m+w<8; and
  • [0020]
    D is H, Cl-C4 alkyl, Cl-C4 alkoxy, C6H5, CH2C6H5 or halogen.
  • [0021]
    Preferred aryl acrylic hydrophobic monomers for use in the materials of the present invention are those wherein A is CH3, B is (CH2)m, m is 2-5, Y is nothing or O, w is 0-1, and D is H. Most preferred are 4-phenylbutyl methacrylate, 5-phenylpentyl methacrylate, 2-benzyloxyethyl methacrylate, and 3-benzyloxypropyl methacrylate.
  • [0022]
    Monomers of structure I can be made by known methods. For example, the conjugate alcohol of the desired monomer can be combined in a reaction vessel with methyl methacrylate, tetrabutyl titanate (catalyst), and a polymerization inhibitor such as 4-benzyloxy phenol. The vessel can then be heated to facilitate the reaction and distill off the reaction by-products to drive the reaction to completion. Alternative synthesis schemes involve adding methacrylic acid to the conjugate alcohol and catalyzing with a carbodiimide or mixing the conjugate alcohol with methacryloyl chloride and a base such as pyridine or triethylamine.
  • [0023]
    The materials of the present invention comprise a total of at least about 80%, preferably at least about 85%, by weight or more of the principal lens-forming monomer.
  • [0024]
    The copolymer materials of the present invention are cross-linked. The copolymerizable cross-linking agent used in the copolymers of this invention may be any terminally ethylenically unsaturated compound having more than one unsaturated group. Suitable cross-linking agents include, for example: ethylene glycol dimethacrylate; diethylene glycol dimethacrylate; allyl methacrylate; 1,3-propanediol dimethacrylate; 2,3-propanediol dimethacrylate; 1,6-hexanediol dimethacrylate; 1,4-butanediol dimethacrylate; CH2=C(CH3)C(=O)O−(CH2CH2O)n-C(=O)C(CH3)=CH2 where n=1-50; and CH2=C(CH3)C(=O)O(CH2)tO—C(=O)C(CH3)=CH2 where t=3-20; and their corresponding acrylates. The most preferred cross-linking monomer is CH2=C(CH3)C(=O)O—(CH2CH2O)n-C(=O)C(CH3)=CH2 where n is such that the number-average molecular weight is about 400, about 600, or, most preferably, about 1000.
  • [0025]
    The chosen cross-linking agent should be soluble in the chosen monomer of structure I to minimize curing problems. When n approaches the upper end of the range of 1-50, the CH2=C(CH3)C(=O)O—(CH2CH2O)n—C(=O)C(CH3)=CH2 cross-linker may not be soluble at desired levels in some monomers of structure I even with the aid of heat or sonication.
  • [0026]
    Generally, only one cross-linking monomer will be present in the device materials of the present invention. In some cases, however, combinations of cross-linking monomers may be desirable. If combinations of two or more types of cross-linking agents are used, none of the cross-linking agents may be CH2=C(CH3)C(=O)O—(CH2CH2O)n—C(=O)C(CH3)=CH2 wherein n =2-50.
  • [0027]
    Generally, the total amount of the cross-linking component is at least 0.1% by weight and, depending on the identity and concentration of the remaining components and the desired physical properties, can range to about 20% by weight. The preferred concentration range for the cross-linking component is 0.1-15% by weight.
  • [0028]
    In addition to the aryl acrylic hydrophobic lens-forming monomer and the cross-linking component, the lens material of the present invention may also contain a total of up to about 10% by weight of additional components which serve other purposes, such as reactive UV and/or blue-light absorbers.
  • [0029]
    A preferred reactive UV absorber is 2-(2′-hydroxy-3′-methallyl-5′-methylphenyl)benzotriazole, commercially available as o-Methallyl Tinuvin P (“oMTP”) from Polysciences, Inc., Warrington, Pa. UV absorbers are typically present in an amount from about 0.1-5 % (weight).
  • [0030]
    Suitable reactive blue-light absorbing compounds are those described in U.S. Pat. No. 5,470,932, the entire contents of which are hereby incorporated by reference. Blue-light absorbers are typically present in an amount from about 0.01-0.5 % (weight).
  • [0031]
    Suitable polymerization initiators include thermal initiators and photoinitiators. Preferred thermal initiators include peroxy free-radical initiators, such as t-butyl (peroxy-2-ethyl)hexanoate and di-(tert-butylcyclohexyl) peroxydicarbonate (commercially available as Perkadoxe® from Akzo Chemicals Inc., Chicago, Ill.). Particularly in cases where the lens material does not contain a blue-light absorbing chromophore, preferred photoinitiators include benzoylphosphine oxide photoinitiators, such as the blue-light initiator 2,4,6-trimethyl-benzoyidiphenylphosphine oxide, commercially available as Lucirin® TPO from BASF Corporation (Charlotte, N.C.). Initiators are typically present in an amount of about 5% (weight) or less.
  • [0032]
    The identity and amount of the principal lens-forming monomer described above and the identity and amount of any additional components are determined by the desired properties of the finished ophthalmic lens. Preferably, the ingredients and their proportion are selected so that the acrylic lens materials of the present invention possess the following properties, which make the materials of the present invention particularly suitable for use in lOLs which are to be inserted through incisions of 5 mm or less.
  • [0033]
    The lens material preferably has a refractive index in the dry state of at least about 1.50 as measured by an Abbe' refractometer at 589 nm (Na light source). For a given optic diameter, optics made from materials having a refractive index lower than 1.50 are necessarily thicker than optics of the same power which are made from materials having a higher refractive index. As such, IOL optics made from materials having a refractive index lower than about 1.50 generally require relatively larger incisions for IOL implantation.
  • [0034]
    The glass-transition temperature (“Tg”) of the lens material, which affects the material's folding and unfolding characteristics, is preferably below about 25° C., and more preferably below about 15° C. Tg is measured by differential scanning calorimetry at 10° C./min., and is determined at the midpoint of the transition of the heat flux curve.
  • [0035]
    The lens material will have an elongation of at least 150%, preferably at least 200%, and most preferably at least 300%. This property indicates that the lens generally will not crack, tear or split when folded. Elongation of polymer samples is determined on dumbbell shaped tension test specimens with a 20 mm total length, length in the grip area of 4.88 mm, overall width of 2.49 mm, 0.833 mm width of the narrow section, a fillet radius of 8.83 mm, and a thickness of 0.9 mm. Testing is performed on samples at standard laboratory conditions of 23±2° C. and 50±5 % relative humidity using a tensile tester. The grip distance is set at 14 mm and a crosshead speed is set at 500 mm/minute and the sample is pulled to failure. The elongation (strain) is reported as a fraction of the displacement at failure to the original grip distance. The modulus is calculated as the instantaneous slope of the stress-strain curve at a selected strain. Stress is calculated at the maximum load for the sample, typically the load when the sample breaks, assuming that the initial area remains constant. This stress is recorded as “tensile strength” in the examples below.
  • [0036]
    IOLs constructed of the materials of the present invention can be of any design capable of being rolled or folded into a small cross section that can fit through a relatively smaller incision. For example, the lOLs can be of what is known as a one piece or multipiece design, and comprise optic and haptic components. The optic is that portion which serves as the lens. The haptics are attached to the optic and hold the optic in its proper place in the eye. The optic and haptic(s) can be of the same or different material. A multipiece lens is so called because the optic and the haptic(s) are made separately and then the haptics are attached to the optic. In a single piece lens, the optic and the haptics are formed out of one piece of material. Depending on the material, the haptics are then cut, or lathed, out of the material to produce the IOL.
  • [0037]
    The invention will be further illustrated by the following examples, which are intended to be illustrative, but not limiting. Example 1: Synthesis of 4-phenylbutyl methacrylate.
  • [0038]
    A three neck round bottom flask containing a teflon coated magnetic stirring bar was successively charged with 120 mL (1.09 mol) of methyl methacrylate (2), 5.35 g (0.015 mol) of titanium tetrabutoxide (Ti(OC4H9)4), 60 mL (0.39 mol) of 4-phenyl-1-butanol (1), and 14.6 g (0.073 mol) of 4-benzyloxyphenol (4-BOP). An addition funnel, thermometer, and a short path still head with thermometer and receiver flask were placed in the flask necks. The flask was placed in an oil bath and the temperature was increased until distillation began. Methyl methacrylate (2) was placed in the addition funnel and was added dropwise at the same rate as the distillate. The reaction mixture was heated for 4 hours and then cooled to room temperature. The crude product was vacuum distilled to isolate 62.8 g (0.29 mol, 74%) of 4-phenylbutyl methacrylate (3) as a clear, colorless liquid. Example 2: Synthesis of 3-benzyloxypropyl methacrylate.
  • [0039]
    A three neck round bottom flask containing a teflon coated magnetic stirring bar was successively charged with 95 mL (0.884 mol) of methyl methacrylate (2), 4.22 g (0.012 mol) of titanium tetrabutoxide (Ti(OC4H9)4), 50 mL (0.316 mol) of 3-benzyloxy-1-propanol (1), and 14.6 g (0.073 mol) of 4-benzyloxyphenol (4-BOP). An addition funnel, thermometer, and a short path still head with thermometer and receiver flask were placed in the flask necks. The flask was placed in an oil bath and the temperature was increased until distillation began. Methyl methacrylate (2) was placed in the addition funnel and was added dropwise at the same rate as the distillate. The reaction mixture was heated for 4 hours and then cooled to room temperature. The crude product was vacuum distilled to isolate 36.5 g (0.156 mol, 49%) of 3-benzyloxypropyl methacrylate (3) as a clear, colorless liquid.
  • [0040]
    Examples 3-29, shown below in Tables 1-4, illustrate of the materials of the present invention. Each of the formulations of Examples 3-29 are prepared as follows. After combining the formulation components as listed in Tables 1-4, each formulation is mixed by agitation and then injected into a polypropylene 25×12×1 mm slab mold. To make slabs, the cavity in the bottom portion of the slab mold is filled to capacity with the formulation and then the top is placed on strictly as a seal. The molds can either be filled under an inert nitrogen or standard laboratory atmosphere. To maintain the mold geometry during curing, spring clamps are used on the molds. The clamped molds are placed in a forced air oven and cured by heating to 70-80° C., holding at 70-80° C. for one hour, then heating to approximately 100-110° C. and holding at approximately 100-110° C. for two hours. At the end of polymerization period, the molds are opened and the cured intraocular lenses or polymer slabs are removed and extracted in acetone to remove any materials not bound to the cross-linked network.
  • [0041]
    Physical property data shown for the cured materials in Tables 1-4 were assessed (according to the methods referred to above). Unless indicated otherwise, all ingredient amounts shown below are listed as % by weight. The following abbreviations are used in Tables 1-4:
  • [0042]
    PEMA: 2-phenylethyl methacrylate
  • [0043]
    PPrMA: 3-phenylpropylmethacrylate
  • [0044]
    PBMA: 4-phenylbutylmethacrylate
  • [0045]
    BEEMA: benzyloxyethoxyethyl methacrylate
  • [0046]
    BEMA: 2-benzyloxyethyl methacrylate
  • [0047]
    BPMA: 3-benzyloxypropyl methacrylate
  • [0048]
    PPMA: 5-phenylpentyl methacrylate
  • [0049]
    BBMA: 4-benzyloxybutyl methacrylate
  • [0050]
    PEO 1000: polyethylene glycol 1000 dimethacrylate
  • [0051]
    PEO 600: polyethylene glycol 600 dimethacrylate
  • [0052]
    PEO 400: polyethylene glyclo 400 dimethacrylate
  • [0053]
    EGDMA: ethylene glycoldimethacrylate
  • [0054]
    t-BPO: t-butyl (peroxy-2-ethyl)hexanoate
  • [0055]
    BPO: benzoyl peroxide
    TABLE 1
    Example Tg
    No. PEMA PPrMA PBMA PEO 1000 EGDMA t-BPO % Elongation (° C.)
    3 85 15 1 304
    4 99 1 1 172 15
    5 85 15 1 753 −10
    6 99 1 1 583 0
    7 85 15 1 619 −24
  • [0056]
    [0056]
    TABLE 2
    Examples
    Component 8 9 10 11 12 13 14
    BEMA 89.9
    PBMA 90.0
    BPMA 94.7 90 99.6
    PPMA 89.7
    BBMA 89.9
    PEO 1000 5.3 10 10.3 10.1 10.1 10.1
    EGDMA 0.4
    t-BPO 1.4 1.5 1.4 1.6 1.6 1.3 1.4
    Tensile strength
    (MPa) 3.37 2.83 2.02 3.07 1.11 6.46 4.195
    % Strain 900 659 515 974 440 815 696
    Young's modulus
    (MPa) 0.67 0.62 0.76 1.02 0.33 1.89 2.00
    100% modulus (MPa) 0.45 0.42 0.51 0.59 0.22 1.07 0.99
    RI (dry) 1.539 1.534 1.533 1.543 1.531 1.541 1.535
  • [0057]
    [0057]
    TABLE 3
    Examples
    Component 15 16 17 18 19 20 21 22 23
    PBMA 89.75 85.02 79.97 94.95 89.82 85.03 94.99 89.89 84.96
    PEO 400 10.25 14.98 20.03
    PEO 600 5.05 10.18 14.97
    PEO 1000 5.01 10.11 15.04
    BPO 0.98 0.96 0.95 0.98 0.95 0.96 1.04 0.95 0.97
    Tensile Strength (MPA) 8.23 8.6 8.74 6.55 6.33 514 6.17 5.62 4.35
    % Strain 444 378 325 881 707 562 1051 875 699
    Young's 6.59 5.78
    modulus (MPA) 5.56 3.85 2.82 1.77 4.05 1.92 1.24
    100% modulus 3.47 3.34
    (MPA) 3.32 2.28 1.55 1.12 2.06 1.12 0.77
    Tg(° C.) 5 4 −1 −1 −5
  • [0058]
    [0058]
    TABLE 4
    Examples (Ingredients shown in % w/w)
    Component 24 25 26 27 28 29 30 31
    BEEMA 99.6 90.0
    PPrMA 85.03 85.00
    PBMA 85.02 84.94
    PPMA 85.06 85.00
    PEO 600 14.97 14.98 14.94
    PEO 1000 15.00 15.06 15.00 10.0
    EGDMA 0.6
    BPO  1.00  1.01  0.99  1.01  1.01  1.01
    t-BPO 1.1 1.2
    Tensile  8.34  4.24  2.67  6.15  3.35  2.05 1.56 1.22
    Strength
    (MPA)
    % Strain   502   486   390   662   582   402 468 294
    Youngs (MPA)  5.48  1.38  0.85  2.41  0.88  0.67 0.32 0.51
    100% (MPA)  3.09  0.96  0.57  1.41  0.63  0.48 0.24 0.36
    Tg (° C.) −23.2 −26.7

Claims (16)

We claim:
1. A polymeric ophthalmic or otorhinolaryngological device material having an elongation of at least 150%, comprising a single device-forming monomer and a cross-linking monomer, wherein the single device-forming monomer is present in an amount of at least about 80% by weight and is an aryl acrylic hydrophobic monomer of the formula
wherein: A is H, CH3, CH2CH3, or CH2OH;
B is (CH2)m or [O(CH2)2]n;
C is (CH2)w;
m is 2-6;
n is 1-10;
Y is nothing, O, S, or NR, provided that if Y is O, S, or NR, then B is (CH2)m;
R is H, CH3, CnH2n+1 (n=1-10), iso-OC3H7, C6H5, or CH2C6H5;
w is 0-6, provided that m+w<8; and
D is H, Cl-C4 alkyl, Cl-C4 alkoxy, C6H5, CH2C6H5 or halogen.
2. The polymeric ophthalmic or otorhinolaryngological device material of claim 1 wherein A is CH3, B is (CH2)m, m is 2-5, Y is nothing or 0, w is 0-1, and D is H.
3. The polymeric ophthalmic or otorhinolaryngological device material of claim 2 wherein the aryl acrylic hydrophobic monomer is selected from the group consisting of 4-phenylbutyl methacrylate; 5-phenylpentyl methacrylate; 2-benzyloxyethyl methacrylate; and 3-benzyloxypropyl methacrylate.
4. The polymeric ophthalmic or otorhinolaryngological device material of claim 1 further comprising one or more components selected from the group consisting of reactive UV absorbers and reactive blue-light absorbers.
5. The polymeric ophthalmic or otorhinolaryngological device material of claim 1 wherein the material is an ophthalmic device material and has a refractive index of at least 1.50.
6. The polymeric ophthalmic or otorhinolaryngological device material of claim 1 wherein the material has a Tg less than about ±25° C.
7. The polymeric ophthalmic or otorhinolaryngological device material of claim 6 wherein the material has a Tg less than about ±15° C.
8. The polymeric ophthalmic or otorhinolaryngological device material of claim 1 wherein the material has an elongation of at least 200%.
9. The polymeric ophthalmic or otorhinolaryngological device material of claim 8 wherein the copolymer has an elongation of at least 300%.
10. The polymeric ophthalmic or otorhinolaryngological device material of claim 1 wherein the device is selected from the group consisting of contact lenses; keratoprostheses; corneal inlays or rings; otological ventilation tubes; and nasal implants.
11. The polymeric ophthalmic or otorhinolaryngological device material of claim 1 wherein the cross-linking component comprises one or more cross-linking agents selected from the group consisting of ethylene glycol dimethacrylate; diethylene glycol dimethacrylate; allyl methacrylate; 1,3-propanediol dimethacrylate; 2,3-propanediol dimethacrylate; 1,6-hexanediol dimethacrylate; 1 ,4-butanediol dimethacrylate;
CH2=C(CH3)C(=O)O—(CH2CH2O)n-C(=O)C(CH3)=CH2 where n =1-50; CH2=C(CH3)C(=O)O(CH2)tOC(=O)C(CH3)=CH2 where t =3-20; and their corresponding acrylates, provided that if the device material comprises two or more cross-linking agents, none of the cross-linking agents is CH2=C(CH3)C(=O)O—(CH2CH20)n—C(=O)C(CH3)=CH2 wherein n =2-50.
12. The polymeric ophthalmic or otorhinolaryngological device material of claim 1 wherein the single device-forming monomer is present in an amount of at least about 85% by weight.
13. The polymeric ophthalmic or otorhinolaryngological device material of claim 1 wherein the cross-linking monomer is present in an amount of about 0.01-15% by weight.
14. The polymeric ophthalmic or otorhinolaryngological device material of claim 1 wherein the aryl acrylic hydrophobic monomer is selected from the group consisting of 4-phenylbutyl methacrylate; 5-phenylpentyl methacrylate; 2-benzyloxyethyl methacrylate; and 3-benzyloxypropyl methacrylate; and the cross-linking monomer is CH2=C(CH3)C(=O)O—(CH2CH20)n—C(=O)C(CH3)=CH2, where n is such that the number average molecular weight of the cross-linking monomer is about 1000.
15. An intraocular lens optic comprising the polymeric device material of claim 1.
16. An intraocular lens optic comprising the polymeric device material of claim 14.
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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060068207A1 (en) * 2004-09-28 2006-03-30 Brewer Science Inc., A Missouri Corporation Curable high refractive index resins for optoelectronic applications
WO2007094664A1 (en) * 2006-02-14 2007-08-23 Procornea Holding B.V. High refractive index monomers and (co)polymers prepared therefrom
US20090043007A1 (en) * 2007-08-09 2009-02-12 Alcon, Inc. Ophthalmic lens materials containing chromophores that absorb both uv and short wavelength visible light
US20090054978A1 (en) * 2006-02-14 2009-02-26 Procomea Holding B.V. Intraocular lenses essentially free from glistenings
WO2010025299A3 (en) * 2008-08-27 2010-06-17 Melder Patrick C Nasal ventilation system and method of using same
US20110202037A1 (en) * 2008-08-18 2011-08-18 Bolger William E Fluid delivery catheter apparatus
WO2012004746A2 (en) 2010-07-05 2012-01-12 Polymer Technologies International (Eou) Refractive-diffractive ophthalmic device and compositions useful for producing same
US8945142B2 (en) 2008-08-27 2015-02-03 Cook Medical Technologies Llc Delivery system for implanting nasal ventilation tube

Families Citing this family (56)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8247511B2 (en) 1999-04-12 2012-08-21 Advanced Vision Science, Inc. Water plasticized high refractive index polymer for ophthalmic applications
US6281319B1 (en) 1999-04-12 2001-08-28 Surgidev Corporation Water plasticized high refractive index polymer for ophthalmic applications
US6723815B2 (en) 1999-09-02 2004-04-20 Alcon, Inc. Covalently-bound, hydrophilic coating compositions for surgical implants
EP1210380B1 (en) * 1999-09-07 2005-03-16 Alcon Inc. Foldable ophthalmic and otorhinolaryngological device materials
US8048155B2 (en) 2002-02-02 2011-11-01 Powervision, Inc. Intraocular implant devices
CA2491319C (en) * 2002-07-16 2010-02-16 Alcon, Inc. Ophthalmic and otorhinolaryngological device materials
US8361145B2 (en) 2002-12-12 2013-01-29 Powervision, Inc. Accommodating intraocular lens system having circumferential haptic support and method
US8328869B2 (en) 2002-12-12 2012-12-11 Powervision, Inc. Accommodating intraocular lenses and methods of use
US7354980B1 (en) 2004-03-12 2008-04-08 Key Medical Technologies, Inc. High refractive index polymers for ophthalmic applications
US8166299B2 (en) * 2004-07-06 2012-04-24 Andrew Christopher Kemshall Secure messaging
US7157538B2 (en) * 2004-08-13 2007-01-02 Alcon, Inc. Covalently-bound, hydrophilic coating compositions for surgical implants
US7446157B2 (en) 2004-12-07 2008-11-04 Key Medical Technologies, Inc. Nanohybrid polymers for ophthalmic applications
CN101563115B (en) 2006-07-21 2013-06-19 爱尔康公司 Low-tack ophthalmic and otorhinolaryngological device materials
US8058323B2 (en) * 2006-07-21 2011-11-15 Novartis Ag Low-tack ophthalmic and otorhinolaryngological device materials
US7714039B2 (en) * 2006-07-21 2010-05-11 Alcon, Inc. Low-tack ophthalmic and otorhinolaryngological device materials
CA2657789A1 (en) * 2006-07-21 2008-01-24 Alcon Inc. Low-tack ophthalmic and otorhinolaryngological device materials
EP2081612B1 (en) * 2006-10-13 2012-11-21 Novartis AG Intraocular lenses with unique blue-violet cutoff and blue light transmission characteristics
ES2349182T3 (en) * 2007-04-30 2010-12-28 Alcon, Inc. UV absorbers for ophthalmic lens materials.
US8968396B2 (en) 2007-07-23 2015-03-03 Powervision, Inc. Intraocular lens delivery systems and methods of use
WO2009015256A3 (en) * 2007-07-25 2009-03-12 Alcon Inc High refractive index ophthalmic device materials
ES2362817T3 (en) * 2007-10-02 2011-07-13 Alcon, Inc. Ophthalmic device materials containing otorhinolaryngological alkyl ethoxylate.
US7858672B1 (en) 2007-10-02 2010-12-28 Alcon, Inc. Methacrylic materials suitable for ophthalmic and otorhinolaryngological devices
RU2010116897A (en) 2007-10-02 2011-11-10 Алькон, Инк. (Ch) Materials for ophthalmic and ENT devices containing alkyl phenol
EP2192934B1 (en) * 2007-10-03 2011-05-04 Alcon, Inc. Ophthalmic and otorhinolaryngological device materials
EP2192933B1 (en) 2007-10-05 2011-05-25 Alcon, Inc. Ophthalmic and otorhinolaryngological device materials
US7888403B2 (en) * 2007-10-05 2011-02-15 Alcon, Inc. Ophthalmic and otorhinolaryngological device materials
US8394906B2 (en) * 2008-02-12 2013-03-12 Aaren Scientific Inc. Ophthalmic lens having a yellow dye light blocking component
JP2011519685A (en) 2008-05-06 2011-07-14 アルコン,インコーポレイテッド High refractive index ophthalmic device materials
US7803359B1 (en) 2008-05-06 2010-09-28 Alcon, Inc. UV-absorbers for ophthalmic lens materials
US7884228B1 (en) 2008-05-06 2011-02-08 Alcon, Inc. UV-absorbers for ophthalmic lens materials
US8043607B2 (en) 2008-07-15 2011-10-25 Novartis Ag UV-absorbers for ophthalmic lens materials
US8236053B1 (en) 2008-10-08 2012-08-07 Novartis Ag 2-amino benzophenone UV-absorbers for ophthalmic lens materials
RU2503667C2 (en) * 2008-11-04 2014-01-10 Алькон, Инк. Uv/visible light absorbers for ophthalmic lens materials
US8293858B1 (en) 2009-01-14 2012-10-23 Novartis Ag Ophthalmic and otorhinolaryngological device materials containing a reactive NVP macromer
US8148445B1 (en) 2009-01-14 2012-04-03 Novartis Ag Ophthalmic and otorhinolaryngological device materials containing a multi-arm PEG macromer
CN102510860B (en) * 2009-07-06 2014-07-02 诺瓦提斯公司 UV/visible light absorbers for ophthalmic lens materials
EP2451875B1 (en) 2009-07-06 2013-08-28 Novartis AG Visible light absorbers for ophthalmic lens materials
CA2769827C (en) * 2009-08-24 2016-09-13 Novartis Ag Ophthalmic and otorhinolaryngological device materials
RU2571085C2 (en) 2010-01-18 2015-12-20 Новартис Аг Visible radiation absorbers for ophthalmic lenses materials
EP2564245A1 (en) 2010-04-29 2013-03-06 Novartis AG Intraocular lenses with combinations of uv absorbers and blue light chromophores
US8362177B1 (en) 2010-05-05 2013-01-29 Novartis Ag High refractive index ophthalmic device materials with reduced tack
CN102946913B (en) 2010-06-21 2015-01-07 诺瓦提斯公司 High refractive index, acrylic ophthalmic device materials with reduced glistenings
WO2012006616A3 (en) 2010-07-09 2012-04-05 Powervision, Inc. Intraocular lens delivery devices and methods of use
ES2531339T3 (en) * 2011-02-08 2015-03-13 Novartis Ag Ophthalmic device materials hydrophobic low adherence
DK2714107T3 (en) 2011-06-01 2015-05-04 Novartis Ag Hydrophobic acrylic materials for intraocular lenses
DK2714108T3 (en) 2011-06-03 2015-04-20 Novartis Ag Hydrophobic acrylic materials for intraocular lenses
JP5799634B2 (en) 2011-07-22 2015-10-28 株式会社リコー Image processing apparatus, an image processing system
WO2013025671A1 (en) 2011-08-15 2013-02-21 Novartis Ag Uv-absorbers for ophthalmic lens materials
KR20140062119A (en) 2011-09-16 2014-05-22 벤즈리써치앤드디벨롭먼트코오포레이숀 Hydrophobic intraocular lens
CA2862795A1 (en) 2012-02-15 2013-08-22 Novartis Ag Ophthalmic and otorhinolaryngological device materials containing a multi-arm peg macromer
US8585938B1 (en) 2012-03-30 2013-11-19 Novartis Ag UV-absorbers for ophthalmic lens materials
KR20150030206A (en) 2012-06-26 2015-03-19 노바르티스 아게 2-amino benzophenone uv-absorbers for ophthalmic lens materials
WO2014106866A4 (en) 2013-01-07 2014-09-25 Council Of Scientific & Industrial Research Flexible, high refractive index hydrophobic copolymer
CA2928011A1 (en) 2013-12-04 2015-06-11 Novartis Ag Soft acrylic materials comprising a poly(phenylether)-containing monomer having a high refractive index and minimized glistening
CN106999628A (en) 2014-12-16 2017-08-01 诺华股份有限公司 Hydrophobic acrylate-acrylamide copolymers for ophthalmic devices
EP3223870A1 (en) 2015-02-16 2017-10-04 Novartis AG Wet-pack intraocular lens materials with high refractive index

Family Cites Families (55)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3850892A (en) 1972-01-03 1974-11-26 Biocontacts Physiologically compatible plastic contact lenses and a method for their production
US4304895A (en) 1973-06-20 1981-12-08 Wesley-Jessen, Inc. Ultraviolet absorbing corneal contact lenses
US4036814A (en) 1974-07-04 1977-07-19 Warner-Lambert Company Lightly cross-linked hydrogel formed from N-vinyl lactam and hydrophobic acrylic ester comonomer
US4260954A (en) 1979-01-26 1981-04-07 Barcus-Berry, Inc. Amplifier load correction system
US4267295A (en) 1979-02-09 1981-05-12 Syntex (U.S.A.) Inc. Polymeric compositions and hydrogels formed therefrom
US4452776A (en) 1979-08-20 1984-06-05 Eye Research Institute Of Retina Foundation Hydrogel implant article and method
JPS6017404B2 (en) 1980-12-15 1985-05-02 Hooya Kk
US4405773A (en) 1982-02-05 1983-09-20 Schering Corporation Hydrophylic contact lenses and methods for making same
US5507805A (en) 1982-05-03 1996-04-16 American Cyanamid Company Intraocular lens and method of retaining in place
DE3376267D1 (en) 1982-11-11 1988-05-19 Showa Denko Kk Polymerizable Compositions
JPS6334447B2 (en) 1983-04-22 1988-07-11 Toyo Contact Lens Co Ltd
US4528311A (en) 1983-07-11 1985-07-09 Iolab Corporation Ultraviolet absorbing polymers comprising 2-hydroxy-5-acrylyloxyphenyl-2H-benzotriazoles
EP0391452B1 (en) 1983-08-30 1994-01-05 Ezekiel Nominees Pty.Ltd. Intraocular lens implants
US4664666A (en) 1983-08-30 1987-05-12 Ezekiel Nominees Pty. Ltd. Intraocular lens implants
CA1252249A (en) * 1983-09-24 1989-04-04 Teruo Sakagami Halogen-containing resin lens material
JPS60200011A (en) 1984-03-21 1985-10-09 Matsushita Electric Ind Co Ltd Liquid fuel burner
US4620954A (en) 1985-06-07 1986-11-04 Ciba Vision Care Corp. Hydrogel from ultraviolet-initiated copolymerization
JPS62111229A (en) 1985-11-11 1987-05-22 Hoya Corp Soft contact lens
US4676792A (en) 1986-08-26 1987-06-30 Donald Praeger Method and artificial intraocular lens device for the phakic treatment of myopia
JPH0622565B2 (en) 1986-10-28 1994-03-30 株式会社メニコン Material for intraocular lens
EP0273710B2 (en) 1986-12-26 1996-10-16 Nippon Shokubai Kagaku Kogyo Co., Ltd Resin having high refractive index, process for producing said resin and optical materials composed of said resin
NL8701548A (en) 1987-07-01 1989-02-01 Tno A polymer network, a process for the preparation thereof, as well as, their use for coating and / or impregnating or for the manufacture of ophthalmic lenses, as well as a molded article, in whole or in part composed of such a polymer network.
US4834750A (en) 1987-09-17 1989-05-30 Ioptex Research, Inc. Deformable-elastic intraocular lens
US5269813A (en) 1990-06-12 1993-12-14 Menicon Co., Ltd. Material for one-piece intraocular lenses
ES2094796T3 (en) * 1990-11-07 1997-02-01 Nestle Sa Polymers and their use in ophthalmic lenses.
US5290892A (en) * 1990-11-07 1994-03-01 Nestle S.A. Flexible intraocular lenses made from high refractive index polymers
JPH05310A (en) 1991-06-26 1993-01-08 Kobe Steel Ltd Wiper device for hot rolling mill and method for controlling the same
US5341974A (en) 1992-06-19 1994-08-30 Mont-Bell Co., Ltd. Back bag
US5331073A (en) 1992-11-09 1994-07-19 Allergan, Inc. Polymeric compositions and intraocular lenses made from same
JP3108550B2 (en) 1992-11-11 2000-11-13 信越化学工業株式会社 Lens material for soft eye
US5470932A (en) 1993-10-18 1995-11-28 Alcon Laboratories, Inc. Polymerizable yellow dyes and their use in opthalmic lenses
US5451651A (en) 1993-12-17 1995-09-19 Bausch & Lomb Incorporated Urea and urethane monomers for contact lens materials
EP0784652A1 (en) 1994-10-06 1997-07-23 Pharmacia &amp; Upjohn Aktiebolag Intraocular lens materials
WO1996040303A1 (en) * 1995-06-07 1996-12-19 Alcon Laboratories, Inc. Improved high refractive index ophthalmic lens materials
US5654350A (en) 1995-06-07 1997-08-05 Johnson & Johnson Vision Products, Inc. Contact lenses with hydrophilic crosslinkers
WO1997024382A1 (en) 1996-01-02 1997-07-10 Pharmacia & Upjohn Ab Foldable intraocular lens materials
US5922821A (en) * 1996-08-09 1999-07-13 Alcon Laboratories, Inc. Ophthalmic lens polymers
JP2000516520A (en) * 1997-05-29 2000-12-12 アルコン ラボラトリーズ,インコーポレイテッド Materials used in glaucoma filtration devices
US5891931A (en) 1997-08-07 1999-04-06 Alcon Laboratories, Inc. Method of preparing foldable high refractive index acrylic ophthalmic device materials
DK1003795T3 (en) * 1997-08-12 2004-05-17 Alcon Mfg Ltd Polymers for ophthalmic lenses
JP4144920B2 (en) 1997-08-20 2008-09-03 興和株式会社 Soft intraocular lens material
JP3641110B2 (en) 1997-08-20 2005-04-20 株式会社メニコン Material for a soft intraocular lens
DE19738345C1 (en) 1997-09-02 1999-05-06 Mdp Medical Device Polymers Gm intraocular lens
CN1213671A (en) 1997-10-07 1999-04-14 参天制药株式会社 Four-component copolymer and eye lens formed by same
ES2243053T3 (en) * 1998-04-15 2005-11-16 Alcon Manufacturing Ltd. Materials index ophthalmic device high refractive prepared using a method of crosslinking after polymerization.
DE69941084D1 (en) * 1998-04-15 2009-08-20 Alcon Inc Material with a high refractive index ophthalmic device
CN1188178C (en) * 1998-04-15 2005-02-09 阿尔康实验室公司 Bicomposite artificial intraosular lens and method for its preparation
EP1137956A1 (en) 1998-10-29 2001-10-04 Allergan Sales, Inc. Intraocular lenses made from polymeric compositions
US6245106B1 (en) 1998-10-29 2001-06-12 Allergan Sales, Inc. Intraocular lenses made from polymeric compositions and monomers useful in said compositions
US6329485B1 (en) 1998-12-11 2001-12-11 Bausch & Lomb Incorporated High refractive index hydrogel compositions for ophthalmic implants
US6281319B1 (en) 1999-04-12 2001-08-28 Surgidev Corporation Water plasticized high refractive index polymer for ophthalmic applications
WO2000079312A1 (en) 1999-06-17 2000-12-28 Bausch & Lomb Surgical, Inc. High refractive index compositions for ophthalmic implants
US6271281B1 (en) 1999-08-26 2001-08-07 Medennium, Inc. Homopolymers containing stable elasticity inducing crosslinkers and ocular implants made therefrom
EP1210380B1 (en) * 1999-09-07 2005-03-16 Alcon Inc. Foldable ophthalmic and otorhinolaryngological device materials
CA2381177A1 (en) * 1999-09-07 2001-03-15 Charles Freeman Ophthalmic and otorhinolaryngological device materials

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060068207A1 (en) * 2004-09-28 2006-03-30 Brewer Science Inc., A Missouri Corporation Curable high refractive index resins for optoelectronic applications
US20090087666A1 (en) * 2004-09-28 2009-04-02 Mercado Ramil-Marcelo L Curable high refractive index resins for optoelectronic applications
WO2007094664A1 (en) * 2006-02-14 2007-08-23 Procornea Holding B.V. High refractive index monomers and (co)polymers prepared therefrom
US7923520B2 (en) 2006-02-14 2011-04-12 Procornea Holding B.V. High refractive index monomers and (co)polymers prepared therefrom
US20090054978A1 (en) * 2006-02-14 2009-02-26 Procomea Holding B.V. Intraocular lenses essentially free from glistenings
US20110021733A1 (en) * 2006-02-14 2011-01-27 Procornea Holding B.V. Intraocular lenses essentially free from glistenings
US9103964B2 (en) 2006-02-14 2015-08-11 Oculentis Holding B.V. Intraocular lenses essentially free from glistenings
US7728051B2 (en) * 2007-08-09 2010-06-01 Alcon, Inc. Ophthalmic lens materials containing chromophores that absorb both UV and short wavelength visible light
US20090043007A1 (en) * 2007-08-09 2009-02-12 Alcon, Inc. Ophthalmic lens materials containing chromophores that absorb both uv and short wavelength visible light
US20110202037A1 (en) * 2008-08-18 2011-08-18 Bolger William E Fluid delivery catheter apparatus
WO2010025299A3 (en) * 2008-08-27 2010-06-17 Melder Patrick C Nasal ventilation system and method of using same
US20110201996A1 (en) * 2008-08-27 2011-08-18 Melder Patrick C Nasal ventilation system and method of using same
US8945142B2 (en) 2008-08-27 2015-02-03 Cook Medical Technologies Llc Delivery system for implanting nasal ventilation tube
WO2012004746A2 (en) 2010-07-05 2012-01-12 Polymer Technologies International (Eou) Refractive-diffractive ophthalmic device and compositions useful for producing same
WO2012004744A2 (en) 2010-07-05 2012-01-12 Polymer Technologies International (Eou) Polymeric composition for ocular devices

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